JPH04230236A - 部分フッ素化ジカルボン酸およびその酸クロリド、それらの製法ならびにそれらの使用 - Google Patents

部分フッ素化ジカルボン酸およびその酸クロリド、それらの製法ならびにそれらの使用

Info

Publication number: JPH04230236A
Authority: JP; Japan
Prior art keywords: bar; formula; compound; acid; oxygen
Prior art date: 1990-06-25
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Pending

Application number

JP3152884A

Other languages

English (en)

Japanese (ja)

Inventor

Freimund Roehrscheid

フライムント・レーアシャイド

Wolfgang Appel

ヴォルフガング・アペル

Guenter Siegemund

ギュンター・ジーゲムント

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Hoechst AG

Original Assignee

Hoechst AG

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-06-25

Filing date

1991-06-25

Publication date

1992-08-19

1991-06-25 Application filed by Hoechst AG filed Critical Hoechst AG

1992-08-19 Publication of JPH04230236A publication Critical patent/JPH04230236A/ja

Status Pending legal-status Critical Current

Links

NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title claims abstract description 6
150000001990 dicarboxylic acid derivatives Chemical class 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 25
239000004305 biphenyl Substances 0.000 claims abstract description 12
239000000203 mixture Substances 0.000 claims abstract description 11
229910017052 cobalt Inorganic materials 0.000 claims abstract description 10
239000010941 cobalt Substances 0.000 claims abstract description 10
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 10
239000011572 manganese Substances 0.000 claims abstract description 10
229910052748 manganese Inorganic materials 0.000 claims abstract description 9
PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims abstract description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
229910052794 bromium Inorganic materials 0.000 claims abstract description 7
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 6
239000002253 acid Substances 0.000 claims abstract description 5
150000002148 esters Chemical class 0.000 claims abstract description 3
238000000034 method Methods 0.000 claims description 25
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 16
239000001301 oxygen Substances 0.000 claims description 16
229910052760 oxygen Inorganic materials 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 14
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 10
229960000583 acetic acid Drugs 0.000 claims description 9
230000003647 oxidation Effects 0.000 claims description 9
238000007254 oxidation reaction Methods 0.000 claims description 9
125000004432 carbon atom Chemical group C* 0.000 claims description 8
239000007789 gas Substances 0.000 claims description 8
229910052684 Cerium Inorganic materials 0.000 claims description 7
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 6
230000002378 acidificating effect Effects 0.000 claims description 6
239000003054 catalyst Substances 0.000 claims description 5
239000012362 glacial acetic acid Substances 0.000 claims description 5
150000003839 salts Chemical class 0.000 claims description 5
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 4
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 4
229910052751 metal Inorganic materials 0.000 claims description 4
239000002184 metal Substances 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
125000004429 atom Chemical group 0.000 claims description 3
229910000042 hydrogen bromide Inorganic materials 0.000 claims description 3
230000001590 oxidative effect Effects 0.000 claims description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 2
PQLVXDKIJBQVDF-UHFFFAOYSA-N acetic acid;hydrate Chemical compound O.CC(O)=O PQLVXDKIJBQVDF-UHFFFAOYSA-N 0.000 claims description 2
239000000835 fiber Substances 0.000 claims description 2
229910021645 metal ion Inorganic materials 0.000 claims description 2
235000019260 propionic acid Nutrition 0.000 claims description 2
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims description 2
ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 2
239000000463 material Substances 0.000 claims 1
150000002763 monocarboxylic acids Chemical class 0.000 claims 1
239000012429 reaction media Substances 0.000 claims 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract description 7
235000010290 biphenyl Nutrition 0.000 abstract description 6
125000000217 alkyl group Chemical group 0.000 abstract description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract description 3
229910001882 dioxygen Inorganic materials 0.000 abstract description 2
150000002762 monocarboxylic acid derivatives Chemical class 0.000 abstract description 2
125000005518 carboxamido group Chemical group 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
-1 Aromatic dicarboxylic acid halides Chemical class 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
150000001991 dicarboxylic acids Chemical class 0.000 description 3
229910000040 hydrogen fluoride Inorganic materials 0.000 description 3
239000007791 liquid phase Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000003960 organic solvent Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
150000001502 aryl halides Chemical class 0.000 description 2
239000002585 base Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical class [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 2
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
239000004215 Carbon black (E152) Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical class [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
229910021585 Nickel(II) bromide Inorganic materials 0.000 description 1
229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
239000004952 Polyamide Substances 0.000 description 1
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
229910001513 alkali metal bromide Inorganic materials 0.000 description 1
SWLVFNYSXGMGBS-UHFFFAOYSA-N ammonium bromide Chemical compound [NH4+].[Br-] SWLVFNYSXGMGBS-UHFFFAOYSA-N 0.000 description 1
229910052786 argon Inorganic materials 0.000 description 1
150000001491 aromatic compounds Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
150000004074 biphenyls Chemical class 0.000 description 1
150000001649 bromium compounds Chemical class 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
150000001768 cations Chemical class 0.000 description 1
MOOUSOJAOQPDEH-UHFFFAOYSA-K cerium(iii) bromide Chemical compound [Br-].[Br-].[Br-].[Ce+3] MOOUSOJAOQPDEH-UHFFFAOYSA-K 0.000 description 1
239000012295 chemical reaction liquid Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000012043 crude product Substances 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
238000001035 drying Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
229910001385 heavy metal Inorganic materials 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
DOTMOQHOJINYBL-UHFFFAOYSA-N molecular nitrogen;molecular oxygen Chemical compound N#N.O=O DOTMOQHOJINYBL-UHFFFAOYSA-N 0.000 description 1
239000000178 monomer Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
IPLJNQFXJUCRNH-UHFFFAOYSA-L nickel(2+);dibromide Chemical compound [Ni+2].[Br-].[Br-] IPLJNQFXJUCRNH-UHFFFAOYSA-L 0.000 description 1
150000002894 organic compounds Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
238000006864 oxidative decomposition reaction Methods 0.000 description 1
239000012071 phase Substances 0.000 description 1
238000005191 phase separation Methods 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920001470 polyketone Polymers 0.000 description 1
239000012264 purified product Substances 0.000 description 1
230000005855 radiation Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C63/00—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings
- C07C63/68—Compounds having carboxyl groups bound to a carbon atoms of six-membered aromatic rings containing halogen
- C07C63/72—Polycyclic acids

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

JP3152884A 1990-06-25 1991-06-25 部分フッ素化ジカルボン酸およびその酸クロリド、それらの製法ならびにそれらの使用 Pending JPH04230236A (ja)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE4020185A DE4020185A1 (de)	1990-06-25	1990-06-25	Teilfluorierte dicarbonsaeure sowie deren saeurechlorid, verfahren zu ihrer herstellung und ihre verwendung
DE4020185:6		1990-06-25

Publications (1)

Publication Number	Publication Date
JPH04230236A true JPH04230236A (ja)	1992-08-19

Family

ID=6409027

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP3152884A Pending JPH04230236A (ja)	1990-06-25	1991-06-25	部分フッ素化ジカルボン酸およびその酸クロリド、それらの製法ならびにそれらの使用

Country Status (4)

Country	Link
US (1)	US5202469A (de)
EP (1)	EP0464471A3 (de)
JP (1)	JPH04230236A (de)
DE (1)	DE4020185A1 (de)

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3355500A (en) *	1964-03-18	1967-11-28	Allied Chem	4, 4'-bis (1, 1, 3, 3-tetrafluoro-1, 3-dichloro-2-hydroxy-2-propyl)-diphenylether
US4339595A (en) *	1980-06-27	1982-07-13	Standard Oil Company (Indiana)	Hexa(meta-,para-carboxyphenyl)benzene compounds
EP0063874A1 (de) *	1981-04-29	1982-11-03	Imperial Chemical Industries Plc	Herstellung aromatischer Polyketone
US4433132A (en) *	1982-09-02	1984-02-21	Polaroid Corporation	Polyesters containing bis(trifluoromethyl)biphenylene radicals
US4716245A (en) *	1985-04-24	1987-12-29	Teijin Petrochemical Industries, Ltd.	Process for producing 2,6-naphthalenedicarboxylic acid
DE3688882T2 (de) *	1986-01-18	1993-11-25	Technochemie Gmbh	Härtbare Harze.
US4863640A (en) *	1986-05-27	1989-09-05	United Technologies Corporation	Monomers for high temperature fluorinated polyimides
US4758380A (en) *	1986-10-29	1988-07-19	The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration	Substituted 1,1,1-triaryl-2,2,2-trifluoroethanes and processes for their synthesis
DE3886078T2 (de) *	1987-04-03	1994-05-05	Daikin Ind Ltd	Fluor enthaltende aromatische Verbindung, Verfahren für ihre Herstellung und ihre Verwendung.
DE3739797A1 (de) *	1987-11-24	1989-06-08	Hoechst Ag	Teilfluorierte dicarbonsaeure sowie deren saeurechlorid, verfahren zu ihrer herstellung und verwendung
US4950786A (en) *	1988-01-19	1990-08-21	Amoco Corporation	Method for making 2,6-naphthalene dicarboxylic acid

1990
- 1990-06-25 DE DE4020185A patent/DE4020185A1/de not_active Withdrawn
1991
- 1991-06-19 EP EP19910110055 patent/EP0464471A3/de not_active Withdrawn
- 1991-06-20 US US07/718,009 patent/US5202469A/en not_active Expired - Fee Related
- 1991-06-25 JP JP3152884A patent/JPH04230236A/ja active Pending

Also Published As

Publication number	Publication date
EP0464471A3 (en)	1992-10-14
DE4020185A1 (de)	1992-01-02
EP0464471A2 (de)	1992-01-08
US5202469A (en)	1993-04-13

Publication	Publication Date	Title
JP2002508343A (ja)	2002-03-19	芳香族カルボン酸の製造方法
JP2744971B2 (ja)	1998-04-28	一部フッ素化されたカルボン酸及びその誘導体並びにその製造方法
CN1980881A (zh)	2007-06-13	制备卤代邻苯二甲酸和卤代邻苯二甲酸酐的方法
JP3959602B2 (ja)	2007-08-15	ビフェニル類の製造方法
JPS6251253B2 (de)	1987-10-29
JPH04230236A (ja)	1992-08-19	部分フッ素化ジカルボン酸およびその酸クロリド、それらの製法ならびにそれらの使用
US7541489B2 (en)	2009-06-02	Method of making halophthalic acids and halophthalic anhydrides
JPS6168444A (ja)	1986-04-08	２，６−ナフタレンジカルボン酸の製造方法
US4827026A (en)	1989-05-02	Method for producing 5-t-butylisophthalic acid
JPH06172260A (ja)	1994-06-21	ナフタレンカルボン酸の製造法
JP3027162B2 (ja)	2000-03-27	ビフェニルカルボン酸の製造方法
JPH04230237A (ja)	1992-08-19	部分フッ素化テトラカルボン酸およびそのジアンヒドリド、それらの製法ならびにそれらの使用
US5274126A (en)	1993-12-28	Partially fluorinated tetracarboxylic acid and the dianhydride thereof, a process for their preparation and their use
EP0323309A2 (de)	1989-07-05	Verfahren zur Herstellung von Naphthalindicarbonsäuren
JP4143295B2 (ja)	2008-09-03	９，９−二置換−２，３，６，７−キサンテンテトラカルボン酸二無水物の製造方法
JPH0768247B2 (ja)	1995-07-26	ジアリ−ルジカルボン酸の製造方法
EP0255384B1 (de)	1991-10-16	4,4-bis(Carboxyphenylsulfonyl)diphenylether, Verfahren zu deren Herstellung und deren Verwendung
JP4678081B2 (ja)	2011-04-27	トリメリット酸の製造法
JPH0243745B2 (ja)	1990-10-01	Torikuroromechirukinokisarinruioyobisonoseizohoho
CN121085779A (zh)	2025-12-09	六氯二甲苯作为新型酰氯化试剂的用途及酰氯的高效制备
JP2509983B2 (ja)	1996-06-26	アニス酸の製造方法
JPH0571573B2 (de)	1993-10-07
JPS6412254B2 (de)	1989-02-28
JPH04230228A (ja)	1992-08-19	部分フッ素化ビフェニル類、それらの製法およびそれらの使用
JPH05186379A (ja)	1993-07-27	フェノールの製法